I recently had a client ask me if it makes sense to rotate security testing firms. "It's something I've always done, but I'm not sure if it really works or not."

I said in my experience, it doesn't really work very well at all.

I run into it less now than I did ten years ago, but there are still quite a few folks out there using a different firm for each annual pentest, or who never use the same firm on the same target more than once and keep a rotating roster of firms in the hopper.

What blows my mind about the whole switch-vendors-every-year mentality is that it's built around the presumption that most pentesters are terrible (plausible, in some cases) and are only going to try hard when you're a new client. There's also a perception that there's no value in building an ongoing relationship with a firm, since everyone does the same things, in the same order, to the same target every time.

On any of our engagements, the first time we look at a given target, we have to ramp up and learn everything we can about it: what mistakes your developers are more prone to make, what misconfigurations you made in your EDR deployment, how to keep from knocking the staging environment offline, which sysadmin knows how to bring it back up. The list goes on and on.

The early phases of a new assessment for a new client are a lot like the first few days on the job for a new employee. You won't really see productive results until they've learned the ropes a bit and have a handle on how things work (and don't work) in your environment.

You need to keep working with a pentest firm once they've ramped up on your environment for the same reason you need to keep employees: they've learned valuable things that someone new would have to relearn, and that's a poor use of time and resources if you have a seasoned person on hand to do the job.

When they wrap that first gig, a good pentester is already thinking about different and better ways to go after the target next time.

On the other side of things, if you're rotating firms over and over, and you don't see any value in follow-on projects, maybe you're not investing in the relationship yourself. Heck, maybe you don't even want to, maybe you just want another annual rotated-firm rubber-stamp assessment to keep the auditors happy. Maybe you're even cynical enough to admit that if you let the same firm hit the same targets two years in a row somebody would finally figure out how to get past the WAF and then you'd have a lot more work to do.

I've had people proudly say to me, "we have new people hit this every year and they find the same bugs". What they don't seem to understand is that it also follows that if you use the same people again, they'll most likely find new bugs. Or, if you really need "fresh eyes", use different resources from a firm you already trust.

To me, the goal of pentesting is to push things forward, or it should be: to iteratively test and improve a little each time, both as attackers and defenders. The best way to do that is to get attackers and defenders collaborating. Building a longstanding working relationship is a great way to do that.